111-50-2Relevant articles and documents
Reaction of convolvine and adipic acid chloride
Okhunov,Aripova
, p. 585 - 586 (2013)
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Self-assembly, binding, and dynamic properties of heterodimeric porphyrin macrocycles
Ballester, Pablo,Costa, Antoni,Deya, Pere M.,Frontera, Antonio,Gomila, Rosa M.,Oliva, Ana I.,Sanders, Jeremy K. M.,Hunter, Christopher A.
, p. 6616 - 6622 (2005)
A series of heterodimeric tetralactam macrocycles have been self-assembled using two kinetically labile zinc porphyrin-pyridine interactions. The stability constants have been determined by UV-vis titrations in CHCl3. The stability constants depend on the degree of preorganization of the linker units connecting the interacting groups. The ability of the self-assembled macrocycles to bind a terephthalamide guest was also investigated. One of the macrocycles was used for the construction of a [2]rotaxane. The dynamic properties of this system provide insight into the exchange mechanisms that operate in complex noncovalent assemblies.
Synthesis of Functional Fluorescent BODIPY-based Dyes through Electrophilic Aromatic Substitution: Straightforward Approach towards Customized Fluorescent Probes
Mirri, Giorgio,Schoenmakers, Dani?l C.,Kouwer, Paul H. J.,Verani?, Peter,Mu?evi?, Igor,?tefane, Bogdan
, p. 450 - 454 (2016)
Fluorescent materials are widely used in biological and material applications as probes for imaging or sensing; however, their customization is usually complicated without the support of an organic chemistry laboratory. Here, we present a straightforward method for the customization of BODIPY cores, which are among the most commonly used fluorescent probes. The method is based on the formation of a new C?C bond through Friedel–Crafts electrophilic aromatic substitution carried out at room temperature. The method presented can be used to obtain completely customized fluorescent materials in one or two steps from commercially available compounds. Examples of the preparation of fluorescent materials for cell staining and functionalization of silica colloids are also presented.
Synthesis and opioid receptor binding affinities of 2-substituted and 3-aminomorphinans: Ligands for μ, κ, and δ opioid receptors
Decker, Michael,Si, Yu-Gui,Knapp, Brian I.,Bidlack, Jean M.,Neumeyer, John L.
, p. 402 - 418 (2010)
The phenolic group of the potent μ and κ opioid morphinan agonist/antagonists cyclorphan and butorphan was replaced by phenylamino and benzylamino groups including compounds with parasubstituents in the benzene ring. These compounds are highly potent μ and κ ligands, e.g., p-methoxyphenylaminocyclorphan showing a Ki of 0.026 nMat the μ receptor and a Ki of 0.03 nM at the κ receptor. Phenyl carbamates and phenylureas were synthesized and investigated. Selective o-formylation of butorphan and levorphanol was achieved. This reaction opened the way to a large set of 2-substituted 3-hydroxymorphinans, including 2-hydroxymethyl-, 2-aminomethyl-, and N-substituted 2-aminomethyl-3- hydroxymorphinans. Bivalent ligands bridged in the 2-position were also synthesized and connected with secondary and tertiary aminomethyl groups, amide bonds, and hydroxymethylene groups, respectively. Although most of the 2-substituted morphinans showed considerably lower affinities compared to their parent compounds, the bivalent ligand approach led to significantly higher affinities compared to the univalent 2-substituted morphinans. 2009 American Chemical Society.
Synthesis, characterization and biological analysis of transition metal complexes with macro cyclic ligands derived from adipic acid, ethylenediamine with diethyloxalate and diethylmalonate
Nishat, Nahid,Bhat, Shahnawaz Ahmad,Kareem, Abdul,Dhyani, Swati,Mohammad, Abdulrahman,Mirza, Azar Ullah
, p. 395 - 409 (2018)
Macro-cyclic ligands from adipic acid, ethylenediamine with diethyloxalate and diethylmalonate and their respective metal complexes of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) with macro cyclic ligands (LO) and (LM) L [N,N′-bis(2-aminoethyl)hexanediamide] were synthesized successfully. These metal complexes were characterized by Fourier transform infrared, ultraviolet visible spectrometry, proton nuclear magnetic resonance spectroscopy, and mass Spectrometry, CHNS and thermogravimetric analysis. The elemental analysis confirms the structures for Mn(II), Co(II) and Ni(II) complexes similar to octahedral geometry, Cu(II) complexes as a square planar geometry and Zn(II) complexes in the tetrahedral geometry. The molar conductivities of all the metal complexes were taken in 10?3?M DMSO, and values of all the metal complexes showed their electrolytic nature which indicates the presence of chloride ions. Thermal analysis supports as the metal complexes are thermally stable. The result of antimicrobial activity against various microorganisms confirms that the metal complexes are potent bactericides and fungicides than the ligand. Metal complexes of LO with Cu(II) and Zn(II) were found to be highly active against S. typhimurium than the complexes of LM. Graphical abstract: [Figure not available: see fulltext.].
Chemoenzymatic Synthesis of Thiazolyl Peptide Natural Products Featuring an Enzyme-Catalyzed Formal [4 + 2] Cycloaddition
Wever, Walter J.,Bogart, Jonathan W.,Baccile, Joshua A.,Chan, Andrew N.,Schroeder, Frank C.,Bowers, Albert A.
, p. 3494 - 3497 (2015)
Thiocillins from Bacillus cereus ATCC 14579 are members of the well-known thiazolyl peptide class of natural product antibiotics, the biosynthesis of which has recently been shown to proceed via post-translational modification of ribosomally encoded precursor peptides. It has long been hypothesized that the final step of thiazolyl peptide biosynthesis involves a formal [4 + 2] cycloaddition between two dehydroalanines, a unique transformation that had eluded enzymatic characterization. Here we demonstrate that TclM, a single enzyme from the thiocillin biosynthetic pathway, catalyzes this transformation. To facilitate characterization of this new class of enzyme, we have developed a combined chemical and biological route to the complex peptide substrate, relying on chemical synthesis of a modified C-terminal fragment and coupling to a 38-residue leader peptide by means of native chemical ligation (NCL). This strategy, combined with active enzyme, provides a new chemoenzymatic route to this promising class of antibiotics.
Chemical generation and modification of peptides containing multiple dehydroalanines
Morrison, Philip M.,Foley, Patrick J.,Warriner, Stuart L.,Webb, Michael E.
, p. 13470 - 13473 (2015)
Chemical formation of dehydroalanine has been widely used for the post-translational modification of proteins and peptides, however methods to incorporate multiple dehydroalanine residues into a single peptide have not been defined. We report the use of methyl 2,5-dibromovalerate which can be used to cleanly carry out this transformation.
Gemfibrozil derivatives as activators of soluble guanylyl cyclase – A structure-activity study
Baker, Hannah,Ferreira, Liam D.,Gayler, Kevin M.,Kane, Robert R.,Karunananthan, Johann W.,Kostyo, Jessica H.,Martin, Emil,Mattke, Jordan,Nguyen, Harold,Plunk, Michael A.,Quintana, Jeremy M.,Sharina, Iraida,Shuda, Mina,Stinchcomb, Alexandra L.
, (2021/08/09)
Previous studies demonstrated that anti-hyperlipidemic drug gemfibrozil acts as NO- and heme-independent activator of NO receptor soluble guanylyl cyclase. A series of new gemfibrozil derivatives were synthesized and evaluated for sGC activation. The structure-activity relationship study identified the positions in gemfibrozil's scaffold that are detrimental for sGC activation and those that are amendable for optimizing modifications. Compared with gemfibrozil, compounds 7c and 15b were more potent activators of cGMP-forming activity of purified sGC and exhibited enhanced relaxation of preconstricted mouse thoracic aorta rings. These studies established the overall framework needed for futher improvement of sGC activators based on gemfibrozil scaffold.
Trityl-containing alcohols—an efficient chirality transmission process from inductor to the stereodynamic propeller and their solid-state structural diversity
Górczyńska, Sylwia,Brzdonkiewicz, Aleksandra,Jelecki, Maciej,Czapik, Agnieszka,Stasiak, Bartosz,Kwit, Marcin
supporting information, (2020/02/18)
The cascade process of a dynamic chirality transmission from the permanent chirality center to the stereodynamic triphenylmethyl group has been studied for series of optically active trityl derivatives. The structural analysis, carried out with the use of complementary methods, enabled us to determine the mechanism of chirality transfer. The process of chirality transmission involves a set of weak but complementary electrostatic interactions. The induction of helicity in a trityl propeller is revealed by rising non-zero cotton effects in the area of trityl UV-absorption. The presence of an additional stereogenic center in close proximity to the trityl-containing stereogenic center significantly affects the sign and, to a lesser extent, magnitude of the respective cotton effects. Despite the bulkiness of the trityl, in the crystalline phase, the molecules under study strictly fill the space. In the crystal, molecules form aggregates stabilized by OH???O hydrogen bonds. However, the presence of two trityl groups precludes formation of OH???O hydrogen bonding. Additionally, the trityl group seems to be responsible for the formation of the solid solutions by e.g., racemates of trans- and cis-2-tritylcyclohexanol. Therefore, the trityl group acts as a supramolecular protective group, which in turn can be used in the crystal engineering.
